In recent years, this surfers’ paradise has undergone a massive transformation, and the evolution of Montauk is still happening. But whether you’re clinging to the past or a beacon of the future, once you cruise onto Old Montauk Highway, it’s difficult not to feel your mind shifting to a chiller gear. With a cool beachfront culture, the crashing waves of Ditch Plains, and the rolling hills around Deep Hollow Ranch, Montauk is a beautiful way to end Long Island.